This paper analyses and discusses different constraints on workplace learning, vocational development and formation of identity. We ask how the learning and development of vocational identities are related to the various learning constraints and restrictions present in the socio-cultural contexts of the workplace. The study utilizes 20 interviews of industrial designers and nursing staff in Finland. The data on the vocational students was collected with Internet questionnaires (N?=?1125) from these two fields; technology and transport, and social services and health care. The results indicated that constraints on learning and professional/vocational identity development at work were mainly social in nature among employees as well as students. Therefore, we suggest that the most necessary conditions for workers' and students' learning are related to the feeling of "weness" that arises from individuals' active participation in the social community.